Methane → 2-(4-Isocyanato-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 245665Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]2)=[CH:4][C:3]=1[O:17][CH3:18].C.Cl[C:21](OC(Cl)(Cl)Cl)=[O:22]>C(OCC)(=O)C>[N:1]([C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:9][C:10]([CH3:12])([CH3:11])[C:13]([CH3:14])([CH3:15])[O:16]2)=[CH:4][C:3]=1[O:17][CH3:18])=[C:21]=[O:22]

Participants

Conditions

Temperature: 70 °C

Procedure

To 4-amino-3-methoxyphenylboronic acid pinacol ester (24.08 mmol, 6 g) and charcoal (0.29 g) in ethyl acetate (50 ml), was added trichloromethyl chloroformate (48.2 mmol, 5.81 mL) and the mixture was stirred at 70° C. for two hours. After cooling to room temperature the solids were removed by filtration and the filtrate concentrated in vacuo to give 6.7 g of 2-(4-isocyanato-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Workup

temperatureAfter cooling to room temperature the solids
customwere removed by filtration
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-5292b91e4fc74c739fc47896a6e775e9
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658794B2

Reaction notes

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